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Date of Award
Master of Science (MS)
O'Neil, Gregory (Gregory W.)
Vyvyan, James R.
Young, Jeff C. (Jeffery C.)
The archazolids are a complex family of natural products with distinct structural features. Inspired by these unique structural characteristics, our group sought to synthesize an analogue of this family, dihydroarchazolid B. We were encouraged to synthesize this analogue due to its high potential to be a potent cytotoxic agent against the vacuolar-type ATPases (V-ATPases) and because it is a simpler analogue than the parent natural products from a synthetic perspective. Within this work, a ring-closing metathesis (RCM) approach was explored in depth towards the completion of our target. From these efforts, a metathesis deactivating stereotriad was uncovered in a key fragment needed for ring closure. Using the knowledge uncovered in our synthetic endeavors, a possible relay-ring closure event is discussed. The synthetic utility of exploring the effects of contiguous remote functionality on alkene reactivity is also demonstrated as knowledge of this type will better inform our future synthetic challenges.
Macrolide antibiotics--Synthesis, Antineoplastic agents--Synthesis, Adenosine triphosphatase, Metathesis (Chemistry)
Western Washington University
Copying of this thesis in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this thesis for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.
King, Brianne R., "Exploring a ring-closing metathesis approach to the archazolids" (2014). WWU Graduate School Collection. 332.